It’s got some bad reviews on Amazon, but Leil Lowndes’s “How to Talk to Anyone” is really solid advice. You can skim over 60% of what she says, and her tone is very annoying (avoid the audiobook!), but every chapter has solid advice on making idle chit-chat with strangers. It’s got a lot of good advice on how to break the ice and keep a conversation going when you can’t think of anything else to say.
The thing to remember about talking with people is that they’re almost always just as awkward as you. You think everyone else is really fascinated with what you did over the weekend, or what city you were born in, while you’re the only one to see through the pointlessness of it? Of course not! That’s boring shit everyone talks about to see if they can get something actually interesting out of you. Everyone is just as terrified as you are of being judged, and you can take advantage of that.